Name: Hira Abid
Student ID: 1010460396
Demo Group: 6 (O)
Extraction Lab Report
Introduction -
The experiment aimed to isolate an active pharmaceutical ingredient contaminated with vanillin
using liquid-liquid extraction and vacuum filtration techniques. It also aimed to identify the
unknown solid compound by melting point determination, obtained IR spectroscopy data, and
provided NMR data. First, by leveraging acid/base chemistry, the unknown API was separated
from impurities (vanillin) by liquid-liquid extraction and then precipitated and re-protonated
from the aqueous layer with an excess of a concentrated inorganic acid (HCl). The precipitated
solid was collected using a Buchner funnel and isolated by vacuum filtration. Finally, melting
point determination, IR, and NMR data allowed for the characterization of the isolated
carboxylic acid, allowing for the analysis of its purity and identification.
Experimental Results - Identification of Unknown API:
My unknown sample was E6. Based on experimental results, the characterization of the
unknown API was likely mefenamic acid. After the API was precipitated and isolated using
vacuum precipitation, a melting point apparatus was used to determine its melting point. The
melting point range of the carboxylic acid was roughly 225 - 230°C which is highly consistent
with mefenamic acid’s range (lit. m.p. 230 - 231 °C).1 Although the melting suggests an
effective purification of mefenamic acid, there may still be some impurities present within the
solid. The isolated solid compound had much moisture present after vacuum filtration which
suggests the presence of slight impurities. Furthermore, the physical appearance of the isolated
and purified carboxylic acid resembled the white powder-like appearance of mefenamic acid.2
Percent Recovery:
Mass of solid started with: 0.209 g
Mass of solid recovered: 0.212 g
% Recovery = (amount recovered/amount started with) x 100%
= (0.209g/0.212g) x 100%
= 98.6%
IR Spectroscopy Data Analysis:
Below is a list of all the functional groups that the major peaks correspond to and a description of
their strength.
● (A) - C-H sp3 → ~ 2980.87 cm-1 , S
● (D) - N-H in amine → ~ 3400 cm-1, w, Br *(the peak did not get labeled however it
appears as an amine N-H bond)
● (B) - C=O in carboxyl group → ~ 1648.03 cm-1, S
● (C) - C=C in aromatic rings → ~ 1575/72/1509.47 cm-1 m
*The broad OH peak is not distinctly visible on the IR spectroscopy which may have been a
result of experimental error or faulty equipment.
H-NMR Spectroscopy Data Analysis:
Mefenamic Acid H-NMR ● Aromatic protons
○ 6.7-8.0 ppm (1H, HB)
○ 6.7-8.0 ppm (1H, HC)
○ 6.7-8.0 ppm (1H, HD)
○ 6.7-8.0 ppm (1H, HE)
○ 6.7-8.0 ppm (1H, HG)
*There are 7 unique 1H integrations however, only 5
signals appear on the H-NMR for the aromatic protons*
● Carboxylic Acid
○ 9.1 ppm (1H, HA)
The carboxylic acid hydrogen appears as a broad peak
roughly around 9 ppm
● Methyls
○ 2.3 ppm (3H, HK)
○ 2.1 ppm (3H, HJ)
The (3H, HK) peak is more deshielded as a result of its
proximity with an electronegative atom, nitrogen;
therefore, it is slightly upfield compared to the (3H, HJ)
peak.
*Amine - The (1H, HF) amine peak is not produced in
the H-NMR.
Isolation and separation of the mixture of benzophenone and 4-hydroxybenzoic acid:
● Add diethyl ether and the mixture of benzophenone and 4-hydroxybenzoic acid
in a conical tube to form the organic layer
● Add water to the tube to form the aqueous layer
● Add NaOH to the tube to separate 4-hydroxybenzoic acid from benzophenone
by deprotonating it and converting it into a carboxylate salt that is now soluble
in water (aqueous layer).
● Use liquid-liquid extraction to transfer the aqueous layer (containing the
carboxylate salt) to another tube so that it can be separated from the organic
layer which contains the undesired compound (benzophenone)
● Add HCl to the tube with the aqueous layer to re-protonate the carboxylate salt
back into 4-hydroxybenzoic acid
Conclusion:
After isolating the unknown API from contaminated with vanillin through liquid-liquid
extraction and vacuum filtration, and then determining its IR spectrum as well as melting point
range, it was concluded that the unknown sample was mefenamic acid. Although impurities were
most likely present, the API’s melting point, physical appearance, and IR and H-NMR analysis
closely align with the properties of mefenamic acid.
Citations:
(1) PubChem. Mefenamic acid. pubchem.ncbi.nlm.nih.gov.
https://pubchem.ncbi.nlm.nih.gov/compound/Mefenamic-acid.
(2)WebMD. Drugs & Medications. Webmd.com.
https://www.webmd.com/drugs/2/drug-11586/mefenamic-acid-oral/details.
